


Bee's 2020 Kinktober Celebration

by neganslucilletblr



Category: Marvel Cinematic Universe, Supernatural, The Punisher (TV 2017), The Walking Dead (TV)
Genre: BDSM, Bottom Dean Winchester, Bottom Sam Winchester, Cock Warming, Consensual Non-Consent, Cuckolding, Daddy Kink, Deep Throating, Dom Dean Winchester, Dom/sub, Drabbles, Exhibitionism, F/M, Feminization, Fingering, Frank Castle - Freeform, Free Use, Glory Hole, Kink, Kinktober 2020, M/M, Multi, Oral Sex, Orgasms, Pegging, Public Sex, Sex, Sex Party, Size Kink, Smut, Somnophilia, Sub Sam Winchester, The Punisher, Top Dean Winchester, Wincest - Freeform, blowjob, collection, handjob, voyuerism
Language: English
Status: In-Progress
Published: 2020-10-06
Updated: 2020-10-31
Packaged: 2021-03-08 02:42:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 8,390
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26858419
Author URL: https://archiveofourown.org/users/neganslucilletblr/pseuds/neganslucilletblr
Summary: Different drabbles for different kinks.Multi-Fandom and multi-character pairings - all drabbles are taken from requests over on my tumblr page. Posting twice a week throughout October
Relationships: Claire Novak/Dean Winchester, Dean Winchester/Sam Winchester, Dean Winchester/You, Frank Castle & Reader, Frank Castle/Reader, Negan/reader, Sam Winchester/You
Comments: 7
Kudos: 109





	1. Somnophilia (Dean x Reader)

**Author's Note:**

> Title: Do Not Disturb
> 
> Kink: Somnophilia - also known as sleeping princess syndrome and sleeping beauty syndrome, is a paraphilia in which an individual becomes sexually aroused by someone who is unconscious.
> 
> Pairing: Dean x Reader
> 
> Tags: sex with someone who is asleep, form of CNC (technically no consent is/can be given), arousal of a sleeping person, fingering, p in v, touch of degradation 
> 
> WC: 800+
> 
> A/Ns: May or may not enjoy being on the receiving end of this…

Y/N always looked so peaceful when she slept. The gentle rise and fall of her chest, the way her eyelids would flutter as she dreamed. Sometimes, Dean found it hard to sleep. If a hunt was too gruelling, or if an unsolved case or getaway monster was plaguing him, Dean would spend the night laying on his side and watching Y/N sleep. It had started innocent enough, but it had turned into something more the longer it went on. At first, Dean started braving reaching out to trail his fingers along her skin, following the dips and curves of her body, over her hips, her waist and up to her breasts. Then as he got more confident, it would become his whole hand. Over time, his touch became a little firmer. But Y/N was a heavy sleeper, or at the very least didn't mind the attention he gave her barely conscious body, because she never disturbed or stopped him. He then started pinching her nipples, watching them get hard and then slowly soften, before making them hard once more. Then, when he built even more confidence, he'd started to encourage her legs apart so he could tease her clit, feel her grow wet beneath his fingertips, even if she wasn't aware of it.

  
  


Even on the nights Dean could sleep, he'd wake up horny, cock hard and pressing against his boxers, and he'd lift Y/N's nightshirt enough to see her bare pussy. She'd started wearing less clothes to bed, usually opting for one of his shirts without panties. Something that told Dean that she knew what he liked to get up to in the middle of the night and she didn't mind. If anything, the way she'd fall asleep on her side, back facing him, one leg thrown over the other so he could see between her legs perfectly, was only even more encouraging. And tonight is no exception.

  
  


Dean smooths his hand over the back of Y/N's thigh, encouraging it to lift higher as it tucks up against her stomach, her other leg straight. It spreads her open beautifully, the low light making her pussy glisten with her arousal, and Dean can't help himself as he trails his hand back down her thigh, over the curve of her ass and lets his fingers slide through her slick, rubbing at her clit and only making her wetter. His free hand pushes into the waistband of his boxers, as he starts to work his fist over his throbbing cock. His fingers dare to dip into her entrance slightly, opening her up, and she's so warm and soft that he can't resist.

  
  


He's never fucked her whilst she's slept before, so he's a little nervous as he pushes his boxers down his legs and spits on his fingers to wet the tip of his cock a little. He shuffles forward and tucks himself up behind her, checking that she's definitely wet enough before he slowly lines himself up with her opening. He watches her face carefully, but it's still that same peaceful look she always has when she's asleep, and so he begins to slowly drive his hips forward, filling her more and more until he's fully seated. He feels her clench around him, and her body moves ever so slightly, but she stays asleep.

  
  


Dean groans almost silently under his breath as he grips her hip and starts to slowly fuck her, watching carefully for any signs of her waking up. His grip slowly begins to tighten on her hip, his thrusts picking up in speed and strength as he gets more and more confident fucking her this way. Y/N murmurs under her breath, turning her face more into the pillow, and she clenches tight around Dean for a second. Dean holds his breath, easing up ever so slightly, until she's definitely asleep again. Dean can feel himself getting closer and closer. She's much tighter this way, and he wonders why he hadn't bit the bullet and done this sooner. The very thought of her waking up and finding him like this, is both terrifying and exhilarating. Dean groans a little louder this time, feeling himself right on that edge, and now soft whimpers are bleeding through Y/N's lips that are growing louder and louder.

  
  


Dean's surprised to feel her hand reach back and grip at his hip, encouraging him deeper and when he looks, her eyes are still closed but he can tell she's awake now, and she knows exactly what's happening. He thought that getting caught would dampen the thrill, that her waking up would end the fantasy, but as she rolls her hips back into him and a nearly silent  _ fuck  _ bleeds through her lips, Dean realises just how arousing this is.

“Sorry, sweetheart, couldn't resist,” Dean moaned, his mouth by her ear. Y/N only moans louder, and Dean smirks, thrusting harder still, only a thrust or two away from his undoing. “Needed to fuck something and you were right there for the taking.”

Y/N gasped for air, her fingernails digging into his hip. “Anytime, baby.” 


	2. Pegging (Dean x Reader)

**Summary for the Chapter:**

> Title: Yes, Ma’am
> 
> Kink: Pegging - Pegging is a sexual practice in which a woman performs anal sex on a man by penetrating his anus with a strap-on dildo. This practice may also involve stimulating the male genitalia.
> 
> Pairing: Dean x Reader
> 
> Tags: use of strap on, anal sex (male receiving), tones of sub!dean, use of anal plug, tones of dom!Reader, mentions of p in v 
> 
> WC: 670+
> 
> A/Ns: Dean would 10000% be into pegging and you can’t convince me otherwise.

“Are you sure you're ready, baby?” you checked. “Been a while since we got to do this,” you reminded him, dragging your nails softly down his torso, feeling his cock try to resist the restrain of cotton as it throbbed slightly under you as you straddled him.

“Fuck yeah,” he gasped out, fingers squeezing at your thighs.

“Sure?” you asked once more.

“Check for yourself,” he smirked up at you with a cocky grin, and you giggled softly, climbing gently off of him to push his boxers down his legs. His cock sprang free, slapping against his stomach softly and dribbling precum there. But that wasn't your focus. Your hand fondled over his balls gently, and then dipped lower, your fingers being met with smooth silicone.

“Oh, you naughty boy,” you giggled softly, pressing harder against the silicone and watching as Dean hissed, arching his back slightly. “How long has this been there?” you teased, starting to pull at the plug so it moved a little.

“Si-since we got back, when I – I showered,” he explained, gasping for air. Biting your bottom lip, you tugged at the plug until it was slowly coming out.

“Nice and ready for me then?” you purred, pushing the plug back in, and then out as you slowly started to fuck him with it.

  
  


Dean's eyes were half lidded as he nodded, his lips shining from when he licked them, and he groaned when you took a hold of the purple silicone strapped to your pelvis and started to softly stroke.

“On your hands and knees, baby,” you encouraged, watching as he eagerly scrambled to do as he was told. You moved yourself to kneel directly behind him, pressing down on his back so he was the perfect height, and then once more fucked him with the plug, watching him stretch to accommodate it. He'd gone for the larger one, meaning he was already beautifully stretched open and ready for you. You left the plug inside as you reached for the lube and worked on slicking your purple cock with it. Dean grumbled softly, reaching with his one hand to wrap it around his cock and pump slowly when you removed the plug completely. You started to press the tip of the toy against his opening, driving your hips forward slowly and gently, watching him take it so well like always. Dean dropped his head lower, and groaned a little louder, his free hand gripping his pillow tightly.

  
  


You rested your hands on his hips as you slid the rest of the toy inside and watched him take a shuddered breath, adjusting to the feeling of being so full all of a sudden. You waited to see his shoulders relaxing before you started to fuck him, easing the toy in and out of him, working on loosening him up enough.

“Fuck baby, looks so hot,” you moaned softly, feeling yourself getting incredibly wet just watching. Dean started to rock back against you, fucking himself on the toy, moaning louder and pumping himself harder. It never took him very long to get to the edge when he was being fucked, and you were watching carefully for all his tells that you needed to stop. “Take me so well, don't you?”

“Fuck, Y/N, feels good,” he admitted, gasping. “Holy fuck.”

“Forgot how good, didn't you?”

“Ye-yeah, shit.”

  
  


Dean's body slumping, his face pressing into the pillow was your cue to pull out.

“On your back baby,” you instructed, tapping his thigh lightly. You were quick to release the harness from around your waist and legs, the straps and toy falling to the bed. You climbed out of it as Dean settled on his back and you moved to straddle him again. He was panting as he looked up at you, a tired, blissed out smile on his plump lips as he watched you line his cock up with your dripping centre.

“Now it's your turn to fuck me,” you smirked.

“Yes, ma'am.”


	3. Feminization (Dean x Sam)

**Summary for the Chapter:**

> Title: Baby Girl
> 
> Kink: Feminization - When a male is made to appear or act, or treated as a female.
> 
> Pairing: top!Dean x bottom!Sam
> 
> Tags: wincest, bdsm themes, dom!Dean, sub!Sam, bondage, use of toys, anal sex, m/m, humiliation, mocking, p in a, edging
> 
> WC: 650
> 
> A/Ns: This was the right amount out of my comfort zone for me to give it a go. I think I did okay! I don’t normally write top!Dean/bottom!Sam but it kinda worked for this somehow.

He looked quite the sight – bound to the bed completely naked, long limbs stretched to each corner and tied with rope. His chest heaved, back arching off the bed, head pressing back into the pillow as he whimpered.

“Please,” he begged out, voice hoarse.

“Please what, baby girl?” Dean smirked, the coo in his voice was mocking, and Sam whimpered again at Dean's choice of moniker.

“P-please, De, I can't take any more,” he choked out. Dean rounded to the end of the bed, standing between Sam's spread legs and he leaned forward, pressing harder against the toy pulsing violently in Sam's slick hole.

“Oh, what's the matter, sweetheart? Can't handle something so big in your tight little pussy?” he pouted.

“Jesus – Dean, please,” Sam groaned, looking down his body at Dean with wide pleading eyes. Dean started to slip the toy out, but slammed it back inside once more, causing Sam to scream out in a mixture of pain and pleasure. The ropes became taut as he tensed, and then relaxed again with him.

  
  


His cock was twitching uncontrollably against his stomach, dribbling pre-cum there and just begging for attention.

“Should I touch your clit? Help you relax around it?” Dean asked, his hand smoothing up Sam's thigh. A strangled gasp for air left Sam's mouth, and he grunted deep in his throat. “How do you expect to take me if you can't even take this?” he mocked. Dean's fingers wrapped around Sam's throbbing length and pumped slowly, making Sam tense harder.

“Need you, De, please – oh fuck, please,” Sam started to beg, bucking his hips up into the touch. Dean couldn't deny he was ridiculously hard watching Sam fall apart like this. Dean reached down for the toy and removed it completely, throwing it down to the floor. Sam whimpered, his whole body shuddering at the loss of the toy and his eyes opened, half-lidded and watery to look at Dean.

“You want my cock, baby?” Dean asked. Sam started to nod, panting heavily. “Want me to stuff that pretty little pussy full whilst I play with your clit?”

“Ye-yes please, oh shit.”

  
  


Dean knelt on the bed, taking himself in his free hand, and worked himself a little, before dropping his hips to line himself up. He watched Sam's face carefully as he pressed against his entrance and started to slowly drive his hips forward. Sam hissed and clenched around him, so Dean jerked his hand a little harder and faster, feeling Sam slowly relax around him enough he could push forward a little harder.

“Such a good girl for me, Sammy,” Dean cooed, reaching up and brushing some of the hair out of Sam's eyes. “So pretty, such a tight little pussy.” Dean let go of his cock and reached across the bed for the wand, turning it on to a low rumble. He trapped it against Sam's cock and his own stomach and then reached up to let one of Sam's hands free. “Hold it against your clit,” he commanded, once Sam was loose. Sam reached for the toy and pressed against his own cock, shuddering at the contact. Dean straightened up, gripping Sam's thighs as he started to fuck into him a little harder.

“Fuck, Dean, I wanna cum so bad,” Sam told him desperately.

“No, not yet, baby girl,” Dean shook his head.

“Dean, please,” Sam begged, a little more demanding this time.

  
  


Just as Sam tried to pull the toy away, Dean gripped his wrist and kept it held there.

“I told you to hold it. You'll cum when I want you to. Until then keep that on your clit whilst I fuck your pussy. Got it, baby girl?” Dean growled. Sam swallowed thickly and gave a tired nod.

“Yes, Sir.” 


	4. Cock Warming (Sam x Reader)

**Summary for the Chapter:**

> Title: Make Yourself
> 
> Kink: Cock Warming - The act of a man slipping his erection into his partner's vagina or ass in order to keep warm - but without regular movement.  
> Pairing: Sam x Reader
> 
> Tags: cockwarming, masturbation, voyeurism, use of sex toy, female orgasms (lots of), mulitple orgasms, overstimulation, p in v, tones of Dom!Sam, minor degradation, mild praise kink
> 
> WC: 938

“I want to watch you make yourself cum.” Sam’s voice cuts through the silence and pulls you back from that very edge of sleep, and when your tired brain finally processes what he’s just said, wetness instantly pools between your thighs. You keep your eyes closed and lick your lips before answering.

“Right now?” you mumble, sleepily.

“Yes.” Sam’s laying on his side, facing you and he reaches up to brush his fingertips down your jaw. You grumble a little - although you’re now undeniably turned on, the thought of waking yourself up and putting the effort into getting yourself off seems exhausting.

“I’m tired,” you complain, finally fluttering your eyes open to look at him.

“You’re horny too, aren’t you?” he presses with a knowing smirk.

“Yes,” you sigh, defeated.

“Then get yourself off for me and you can go back to sleep.”

The authority in his tone is only making you wetter, so you bite the bullet and roll onto your back, reaching under your bed for your newest toy. You place the toy down next to you and reach under Sam’s shirt you’ve worn to bed to slide your panties down your legs. Dropping them to the floor, you spread your legs and grab the toy again, turning it on to the lowest setting and feeling it rumble in your palm. Sam props his head up onto his elbow as he continues to lay next to you and watch as you press the head of the toy to your clit. You instantly whimper, and move the toy around until you’ve found your sweet spot. You hit the button to turn the intensity up a few notches, and bite down on your bottom lip as the pleasure pulses through your body. You’re already close - the new toy was definitely a good purchase.

You lift your hips off the bed slightly, and your back arches as the pulsing from the toy sends waves of pleasure through your whole body. You can tell you’re on the brink, when you feel Sam’s fingers slip between your legs and tease at your dripping entrance.

“C’mon, I told you to cum for me,” he urges, impatiently. You moan, coming undone around nothing as he continues to rub his fingers around your slick, and he hums in approval as you put on a show for him. “Good girl,” he purrs. You’re panting heavily as you come down, but before you can remove the toy, Sam speaks up again, “cum again for me.” You’re well and truly awake now, the orgasm only making you crave more, and you no longer would have any objection to Sam flipping you over and fucking you into the mattress.

You bite your bottom lip and comply, turning the toy up another notch or two, and basking in the sensation until you’re cumming hard once more. As you’re coming down from your second high, the toy now off and at your side again, Sam quickly pushes his boxers down, throwing them to the floor and he climbs between your legs. His cock is rock hard as he rubs it against your core, catching your clit. You gasp for air, so desperate to feel him inside of you. Sam lowers his face to yours and he presses his mouth to your ear.

“I’m not gonna fuck you, but I do wanna feel your pussy around my cock.” You moan loudly at the very idea, and Sam pulls back slightly, lining himself up and pushing his way inside. You stretch to accommodate him beautifully, feeling him pulse inside your sensitive cunt.

“Couldn’t resist feeling you,” he groans, holding himself deep inside and not moving. You were sort of expecting him to be kidding about not fucking you, but Sam remains unmoving and smirks down at you. “Cum for me again,” he commands. “Wanna feel you cum around my cock.” You whimper as you scramble for the toy and turn it on again, ramping up the intensity to almost full, before pressing it down to your clit and inhaling sharply. You’re instantly close, clenching around his unmoving cock and practically seeing stars. “C’mon, baby,” he encourages. Fuck, you’re right _there_ , gripping around him like a vice as you get nearer and nearer to that edge, and then… “Fuck, that’s it baby,” Sam groans as you come undone.

You’re about to pull the toy away, but another wave is coming and the high you were about to fall down from returns and you’re coming undone again.

“Fuck, making my cock so fucking wet, baby girl,” Sam growls, still holding himself so goddamn _still._ You cum yet again around him, your mind going fuzzy, and all you can concentrate on is the next orgasm about to hit you, there’s barely ten seconds between them as you spasm around him, and your legs shake either side of his hips. “Good girl, such a good little slut for me,” Sam purrs, stroking your face as you finally find the sanity to pull the toy away. If you left it there any longer, you’re worried you’d have passed out from an overload of sensation. “You’re so fucking wet, sweetheart. Shit, feels good.” You whimper up at Sam, eyes heavy and lips parted as you try and calm down.

Sam reaches down for the toy himself and turns it on, handing it back to you.

“Make yourself cum again,” he orders, pushing that final inch of himself that doesn’t normally fit inside you. You moan as he throbs, but still doesn’t move, and the smirk that curls over Sam’s face tells you he’s nowhere near done with you.


	5. Free Use (Frank Castle x Reader)

**Summary for the Chapter:**

> Title: Dinner Time
> 
> Kink: Free Use - A fetish where someone is allowed to fuck any part of their partner at any time.  
> Pairing: Frank Castle x Reader
> 
> Tags: annoyed!Frank, sex whilst doing something mundane, p in v, orgasms, creampie
> 
> WC: 666
> 
> A/Ns: It was nice to give this guy some love again <3

The water starts boiling around the pasta as you finish cutting the pepper and scrape it into the frying pan alongside the rest. You move onto the mushroom as you hear the front door slamming open and then closing again. Frank’s home. He’s clearly in a bad mood, which can only mean one thing. You feign ignorance all the same as you continue to concentrate on making dinner, setting to work on chopping the mushroom in front of you.

“Hey baby, rough day?” you ask carefully, glancing at him as he frowns in the doorway. “Could say that,” he agrees, pushing off the frame and heading towards you. 

“Dinner will be about twenty minutes,” you tell him softly. Frank pushes up behind you, trapping you between him and the counter, and you continue to chop the mushroom as he kisses your cheek and his hands move to unbutton your jeans, and push them and your panties down to your knees. 

You try to keep your breathing regular and the moan out of your voice, feeling your entire body flush with arousal. You can hear his own belt jangling, the zipper on his jeans as he undoes them. 

“Do you want tomato sauce or -” you can’t help the grunt that leaves your lips as you feel him press against your entrance and enter you quickly, “ - or cheese sauce?” you finish. Frank’s hands grip at your hips hard as he pulls you back.

“Cheese,” he growls, before slamming back inside. You moan, your hand tightening around the knife as you try to focus on the task at hand, and not the way Frank’s cock is dragging in and out of you, nudging at your sweet spots over and over again. Frank grunts under his breath, bringing his mouth down to bite your shoulder, and you whimper. 

Your fingers grip at the counter for a moment, your eyes rolling as he fucks you hard and fast, fucking away the stress of his day. You reach for the chopped up pieces of mushroom and drop them into the pan, grabbing another one to cut as your hips and thighs knock into the kitchen counter, starting to make the skin tender. You don’t mind - hearing Frank moaning and cursing under his breath as he chases his release. You continue to chop the mushrooms and rock your hips back into him, humming happily as his one hand leaves your hip to smooth up your body, gripping at your chest as he licks, bites and sucks the back of your neck. You start to roll on the balls of your feet, making him nudge that sweet spot, until your legs are shaking and you’re close. Over the years Frank has been given free use of your body, you’ve become an expert at being able to function at normal things whilst on the brink of orgasm, and cooking dinner is no exception. You’re able to cut and peel and stir like there isn’t a cock buried to the hilt inside you, like you’re not seconds away from coming undone. 

Frank is unrelenting, telling you just how good you feel, how tight and wet and _perfect_ you are around his cock as he leaves finger shaped bruises on your skin, and your climax finally hits you. Your legs nearly buckle, but the way Frank has trapped you stops you going anywhere, and you break concentration from the food for a moment as you come down from your high. As soon as you’re able to, you compose yourself and finish adding the last of the ingredients to the frying pan. 

“Fuck, baby, gonna cum so fucking hard in that pussy,” he growls, pushing himself deeper. You whimper as he stills, shooting his orgasm deep inside, before slowly pulling out and leaving you dripping. He kisses the back of your shoulder, and helps you get your panties and jeans back up your legs. “I’m gonna clean up for dinner,” he tells you. “Can’t wait, it smells good.” 


	6. The Fuckin' Performance (Negan/Dean/Sam x Reader)

**Notes for the Chapter:**

> Title: The Fuckin’ Performance
> 
> Kink: Public Sex, Performance Kink, Glory Hole
> 
> Pairing(s): Negan x Reader, Dean x Reader, Sam x Reader
> 
> Tags: dub con hinted, deep throating, blowjob, training, public sex, glory hole, sex party, voyeurism, forced exhibitionism
> 
> WC: 1337
> 
> A/Ns: I got this idea after reading three of my requests. They kinda formed together in my mind to create this. Enjoy <3

His grip on your hair tightens as he keeps you there and your eyes begin to water, but you blink up at him, waiting for him to pull back. He does eventually, spit dribbling indignantly from your puffy lips, and your fingers that had been digging into his thighs loosen their grip. 

“That’s my good fuckin’ girl,” he praises, leaning down to dry your lips with his thumb. “Didn’t gag that time, you’re fuckin’ getting there,” he smirks, and your chest swells at the validation. “Once more, c’mon, sweetheart.” He straightens up, his grip on your hair tightening once more as he uses it to force your mouth back down on his cock, until your nose is hitting his pubic hair and he’s grunting. You can feel the bulge in the back of your throat, feel how red raw it is from the constant abuse, but maybe you’re finally good enough that you didn’t need to do this training anymore - not that you know why you’re training in the first place. When Negan pulls back a second time he groans and his chest heaves with his heavy breath, and he looks down at you with a shit eating grin before saying, “yeah, I think you’re fuckin’ ready, baby girl.”

-

The music is fairly loud, but the room you’re in has muffled it somewhat, you can no longer hear what lyrics the singer is singing, but you can still hear the bass, feeling it vibrate the floor beneath your knees. You’re given a bottle of water and drink it down eagerly, feeling your throat smart with each gulp, but you’re just grateful for something new. You’re handed a towel next and look up at Negan, smiling gratefully as you take it from him and dry your lips. 

“Almost time for another one, doll,” he chirps, handing you your lipstick next. You didn’t know what you were expecting when Negan had told you that you were ready for something, but it wasn’t this. You didn’t get to see very much of the party, as you were led straight into this room, but from what you did see, there were men sitting around with next to naked girls draped over them, so you assume you’re at some kind of sex party. You hear men’s voices outside, and know it’s your cue as you hand Negan back your lipstick and resume your position, kneeling in front of the wall. 

“I wanna go first,” you hear the other side of the wall. 

“Dude, I’m older, I get to go first,” the other replies, his voice a little deeper. “Let me show you how it’s done.”

“Dean, I’ve done this before,” the other complains. 

“Great, then you can wait outside,” _Dean_ replies. “C’mon Sammy, beat it.” You hear the door opening and closing, and wait for the same thing that’s been happening all night. The guy, who you assume from the conversation is Dean, chuckles to himself and you hear the sound of a belt and then a zip. Before you know it, the hole in front of your face is being filled and you’re suddenly face to face with a hard, thick cock. It’s the first time all night you’ve been impressed by the size and look of one. Negan’s gifted in that department, and it’s what you’ve grown used to, but the guy in front of you could give him a run for his money. 

Negan kicks your leg softly as if to prompt you and you immediately reach up and wrap your hand around it, guiding it towards your lips. You start gently, just like Negan showed you in your training, swirling your tongue around the spongy tip and tasting the now familiar tang of pre-cum, closing your lips around the tip and sucking softly. Dean groans deeply, and seems to thrust further forward, so you know you must be doing a good job. You listen to Negan leaving, knowing that he’ll be back before the next guy comes in. You return your focus to Dean and take him a little deeper, sucking a little harder as he continues to grunt and moan softly on the other side of the wall, and you let your mind wander to what he might look like. Judging from his deep rumbly voice he’s not too young, but he’s also not as old as some of the other men have sounded, he _sounds_ attractive. You paint a picture of some hot man in your mind as you continue to suck him down, until he’s cumming hot and salty down your throat. 

_Sammy_ is next. Dean tells him he’s in for a treat as he leaves, and once again Negan is at your side with water, a towel and your lipstick as you quickly refresh yourself. Your throat is so sore now, it’s almost numb, and you want to ask Negan how many more men you have to serve this way, but you don’t want anyone else to hear you. You once again hear the tell tale signs that the hole in the wall is about to be filled, and sure enough it is. This erection sticks out longer than others, length is clearly on this guys’ side, and you take a moment before reaching up and starting your work. It’s like second nature at this point, taking him as deep as possible. But you’re struggling more than usual, thanks to his extra inch or two that he’s got on all the other men, and Negan has to push on your head to encourage you to take him deeper.

 _Sammy_ groans and curses under his breath, so you know he must be enjoying himself, which is the main thing, and Negan eventually leaves you alone once more to do your supposed job in peace. 

“Fuck, baby, Dean was right, you are good at this,” he grunts, thrusting into your mouth to aid you. You moan softly around him, and between him and Dean, you can feel yourself growing wet, because you’re more hopeful than ever that these two men are attractive. You just can’t help yourself. You grow more eager and listen as his breathing gets harder until eventually he’s shooting his climax into the back of your throat, just like Dean had done. You pull back and wipe your mouth dry. “Thanks,” he tells you breathlessly. The door opens and you see Negan enter, but this time he doesn’t have the usual equipment to freshen you up. He reaches down for your arm and hauls you to your feet as you feel the blood return to them. 

“C’mon baby,” he encourages, pulling you out of the room and down the corridor. You’re being dragged past a group of men that are standing in a line, and Negan barks at some girl he calls Fliss to take your place. You’re taken into a large room with many couches around that are all occupied by men and scantily clad girls, and there’s a large footstool in the centre of the room, which is exactly where Negan leads you. Suddenly, all eyes are on you and the room gets quieter. 

“As is fuckin’ tradition, I’m gonna break in my new girl right fuckin’ here for all of you dirty fuckers to see,” Negan announces loudly, pushing you closer to the stool. It’s large enough to fit you on completely and you hug yourself as you turn to look at him, wondering what he’s got in store for you. Besides the blowjob lessons, Negan hasn’t done anything else with you before. “By now, most of you will have fuckin’ experienced that talent fuckin’ mouth I’ve been crafting for a few weeks. And I’ve got a funny fuckin’ feeling that you’re all gonna wanna piece of this cunt when you see how fuckin’ well she takes it. I know a fuckin’ whore when I see one.” Negan winks at you. “So, sit back and enjoy the fuckin’ performance. Sweetheart? Why don’t you fuckin’ take those clothes off, and let me show off my fancy new fuckin’ toy?”


	7. Primal Kink (Sam x Reader)

**Notes for the Chapter:**

> Title: The Prey
> 
> Kink: Primal Kink
> 
> Pairing: Sam x small!Reader
> 
> Tags: this isn’t A/B/O but it does have that kind of dynamic as that’s what primal kink is all about, alpha!Sam, alpha!reader, hunting, chasing, hunter/prey, fighting for dominance, scratching, biting, rough, animalistic noises
> 
> WC: 850 
> 
> A/Ns: Look out for the “dark version” (Serial killer!Sam) of this drabble which is coming soon! This isn’t exactly like the request, but this is what kinda came to me. The reader in this is described as being short and slim as it plays into the narrative of the request <3

**_Sam’s POV_ **

  
  


The leaves and twigs crunched beneath his feet, and the scents of the forest confused him for a moment so he stopped, drawing a deep breath to regather his senses. He closed his eyes listening for movement, for  _ something,  _ but she’d clearly stopped. He turned as slowly as possible to try and shift his focus to the entire forest surrounding him. He wished he had super scent so he could sniff her out, wished he had sensitive hearing so he could hear her heartbeat. He’d always underestimated her. She was so much smaller than him, always seemed so weak and fragile and he’d almost scoffed at her idea of playing this cat and mouse game. He naively thought he’d have caught her by now, flung her over his shoulder so he could take his prey home a winner. He had never banked on her outsmarting him. He opened his eyes again and started to slowly scan the woodland, looking carefully behind trees and bushes for any sign that she was there. 

A snapping twig causes him to spin around in an instant, but he sees nothing. Sam grunts, a whole lot frustrated and even more aroused by the very idea that she’s this smart. He’s about to start moving again when he sees her, stepping out from behind a trunk and smirking at him tauntingly. Sam’s jaw clenches, his eyes narrowing as she bites down on her bottom lip. 

“Run,” he commands, and she does, speeding off in the other direction and he hears and sees trees and branches moving and breaking as she passes. He gives her a moment before he chases after her, feeling his heart thumping and his adrenaline at an all time high, he can just about see the flash of Y/H/C hair through a break in bark as he runs in pursuit of her, but then it’s gone again, and once more the whole forest falls silent. 

Sam whistles, hearing it echo through the trees, goading her to show herself again, and he looks around as he waits for her to show herself, knowing she won’t be able to resist before long. He whistles again, turning his body to check out a different part of the woodland, but like before it seems he’s alone. He clicks his tongue and waits patiently. He’s stood in the clearing for barely a few seconds before he feels arms wrapped around his throat from behind, a body pouncing on his back and a high pitched growl in his ear. He feels himself stumble and  _ somehow,  _ the girl almost half his size has managed to get him onto the floor and on his back. She straddles him and pins his wrists above his head triumphantly. 

“Didn’t think you were the hunter did you,  _ sweetheart _ ?” she smirked. 

Sam grunted, pushing up and rolling them over so her back is thudding against the forest floor. 

“I’m  _ always  _ the hunter,” he warned with a growl. She giggled, a slight whimper escaping her lips and she managed to fight him off enough to sit up, bringing her face close to his.

“Funny, because I swear I was just the one that got  _ you  _ on the floor,” she taunted. Sam purred deep in his chest, feeling himself getting hard at the glint in her eyes. He reached for her shirt and tore it clean in half, but it only made her giggle again as she reached up and wrapped a small hand around his throat, squeezing. Sam smirked at her attempt and continued to undress her roughly, pulling her shorts roughly down her legs. 

Leaning down, he sunk his teeth into her shoulder, working on undressing himself from the waist down, enough to get his erection free as Y/N’s hands started to scratch down his chest. Sam growled into the bite and forced her legs apart, making her whimper, and pushed her so she was laying flat on the floor once more. Y/N was strong enough to flip onto her front as she attempted to crawl away, but Sam was quick to grip her hips and pull her back towards him. She growled, clearly frustrated and reached back, scratching hard and deep across his hip. Sam hissed at the pain and felt his cock throb. She turned herself over again, ending up on her knees as she knelt directly in front of him, and the two of them panted as they stared at each other. 

Dirt had appeared on both their skins, leaves and twigs caught in Y/N’s hair, and no doubt Sam’s too as they both stared each other down in a silent fight for dominance. Y/N pounced on him, sending Sam crashing backwards and grunting as his bare back thudded against rough ground. Y/N was quick to straddle him, her nails digging into his pecs as she smirked down triumphantly and reached between them to claim her prize and Sam let her, surrendering completely. Something about seeing Y/N like this was so  _ hot.  _ Maybe for once he could learn to be the prey. 


	8. Size/Daddy Kink (Dean x Claire)

**Notes for the Chapter:**

> Title: Playing Daddy
> 
> Kink: Size Kink - Being turned on/aroused at a distinct difference in size in comparison to your partner. Usually includes height, muscle size, penis size, and weight.   
> Daddy Kink - Being turned on/aroused being called or calling someone (usually male) Daddy in a sexual context.
> 
> Pairing: Dean Winchester x Claire Novak
> 
> Tags: angst, tension, smangst, daddy kink, size kink, thigh riding, choking, face fucking, fingering, p in v, dirty talking
> 
> WC: 1200
> 
> A/Ns: Has this been written before? Probably. Do we need more? Probably. So am I gonna write it again? Yes. 

Dean kicks the door open, watching it bounce off the wall, and it’s about to slam closed again from the brute force he’d used to open it in the first place, but his hand comes out to stop it, and he storms into the room, eyes seeking out the target of his anger. 

“Are you fucking stupid?!” he hisses, when the door bounces off the wall yet again, and this time slams shut behind him. The blonde in front of him takes a deep breath and rolls her eyes, her arms instinctively crossing over her chest in defence. 

“I’m alive, aren’t I?” she retaliates. 

“Barely. Claire do you know how dangerous that was? You can’t just storm into a vamps nest on your own,” Dean growls. “You’re lucky that me and Sam found you or-” 

“Or what? I might’ve died? Like you’d care anyway, I’m just an inconvenience, aren’t I?” she presses. 

“No one ever said that,” Dean huffs. 

“You don’t have to, Dean,” she spits back. 

“What’s  _ inconvenient, _ ” Dean starts to explain as calmly as possible, but the anger is still laced in his tone, “is when you don’t listen and try and do stupid shit on your own, to what? Prove you’re a big girl?” Dean scoffs. 

“I am a big girl,” she defends.

“You’re not coming on any more hunts,” Dean tells her adamantly. 

“Fuck you, Dean. You’re not my father, you can’t tell me what to do.”

“No, but you fucking need one,” Dean growls.

“And whose fault is that?” she shouts back. Dean grits his teeth and shakes his head, not wanting this argument again. “Position’s open if you want to play ‘Daddy’,” she adds tauntingly. She steps up to him and glares slightly. “And I  _ am  _ a big girl, I can take care of myself.” 

Dean’s quick to wrap a hand around her throat and press her up against the wall, making her whimper. 

“Don’t look so big to me, sweetheart,” he murmurs through gritted teeth as he holds her there. His aim was to prove to her that she’s not quite as good as she thinks she is, easily able to get overpowered and Dean’s barely broken a sweat, but now as he holds her there and she looks up at him with her lips slightly parted, and her eyes wider as she claws at his wrist, he can feel the pent up anger morphing into something more - something it shouldn’t - but he’s too far gone to care. “Could break you right now if I wanted to,” he tells her, his voice a little lower. She struggles against him, and he pushes a thigh between her legs. She suddenly stops her fight and whimpers. “Maybe you do need someone with a firm hand,” he ponders. 

“Someone like you, you mean?” She asks, gasping for breath. “ _ Daddy _ ,” she adds with a smirk curling her lips. Dean growls and leans down, kissing her roughly. His entire hand is big enough to engulf her neck, and grip at her jaw to keep her head still all at once, and she begins to grind herself down into his thigh desperately. He pulls her away from the wall and uses his grip on her neck to shove her towards the bed. Claire whimpers stumbling backwards, and then smirks, composing herself as she straightens up at the foot of the bed. She unbuttons her flannel just as quickly as Dean does, and as he rips his t-shirt over his head, Claire reveals her little black bra. Dean’s eyes are scanning her hungrily as Claire bites down on her bottom lip, relishing in the attention, and starts to unbutton her jeans. Dean does the same, tearing into his own, but keeping them loose around his hips as he steps forward. 

Claire reaches for his hand and brings it to her chest, encouraging him to squeeze.   
“See, Daddy? A big girl,” she hums. Dean growls, pushing her down onto the bed, and reaching for her jeans as he tears them and her panties down her legs. He straddles her slender body, knees tucked up either side of her chest, and he grips the back of her head with one hand and fists his hard cock free with the other. Her eyes widen when she sees it, and Dean smirks. 

“Still think you’re a big girl? Think you could handle Daddy in that tight little cunt?” he asks, tapping his tip along her kiss-swollen lips. She nods fervently. “Better get it nice and wet first, make sure it slides right in,” he encourages. She opens her mouth as wide as possible, the girth of Dean’s cock stretching her lips, and Dean slowly thrusts to the back of her throat until he’s making her gag. He uses the grip on her hair to bob her mouth up and down his length as he reaches behind him and his fingers find the wet heat between her legs. Claire moans around him when he circles her clit and teases his fingertips around her entrance.  _ Fuck _ , he guessed she’d be tight, but she’s clamping hard around just one finger. 

Dean knows he can’t hold off for long, so he pulls back and moves himself down the bed, kneeling between her legs as he tries to work on opening her up with his fingers. She’s barely managing two when he attempts three, and she mewls and palms at her own breasts as she leans back and watches him. Dean leans down and spits onto her cunt, working the extra slick around her hole and then he smoothes some over his length too. He shuffles a little on his knees and presses against her entrance. 

“If you’re such a big girl, you’ve done this before, right?” Dean checks, glancing up her body to her face. She scoffs, like she’s insulted by the question. “So you’ll take all of Daddy, won’t you? No fuss?” he checks, pushing forward ever so slightly. She hisses and her body’s jerk reaction makes Dean’s cock twitch. “What’s the matter, sweetheart? Daddy’s cock too big?” he taunts. “Awfully quiet now you gotta put your money where your mouth is and act like a big girl, aren’t ya?” He smirks. 

“Please, Daddy,” she begs, rolling her hips down, managing to get the first inch inside. Dean groans at how tight and hot she feels around him, and his eyes flutter closed for a moment. He shouldn’t be doing this but - fuck - forbidden fruit and all that. He thrusts forward until he’s as deep as he can go, Claire whimpering so loudly, if it wasn’t for the way she’s rotating her hips encouragingly, Dean might worry it’s too much for her to handle. He pulls back ever so slightly and leans over her, changing the position and looking down their bodies to see just how wet she makes his cock every time he pulls out. 

“Jesus, baby, feels so good,” Dean gasps, and from this angle he can see the bulge of his tip at the base of her stomach every time he’s fully seated, and  _ fuck  _ he wants to shoot his load deep inside her already. “Should’ve played Daddy a long time ago, huh?” he prompts with a smirk. 

“Fuck, yes, Dean,” Claire moans, throwing her head back. “Best Daddy I’ve ever had.” 


	9. Cuckolding (Sam/Dean x Reader)

**Summary for the Chapter:**

> Title: A Show for the Cameras  
> Kink: Cuckolding - When a man watches his wife or girlfriend have sex with another man.  
> Pairing: Sam x Reader // Dean x Reader  
> Tags: cuck!Sam, cheating (sort of), seduction, flirting, voyeurism, exhibitionism, male masturbation, blowjob, p in v  
> WC: 1217  
> A/Ns: This will be my last Kinktober as it’s now November (lol) and I’m busy! Hope you’ve enjoyed them <3

**_Sam’s POV_ **

_ You need to see this  _

There’s a video file attached to Dean’s email as it sits in Sam’s inbox, and Sam shifts in his office chair and looks up at his door to make sure it’s closed. Most of the firm have gone home for the night, anyway. He sighs as he clicks on the link, and he suddenly realises that it’s security footage from inside Y/N’s office, only down the hall from Sam, but she’s currently not in it - she’s at some corporate meeting for one of her clients. Sam notes the timestamp is from the day before, around seven in the evening. Y/N had stayed on late to work on a case and she didn’t arrive home until almost nine in the end, flustered and clearly in her mind about something. Sam didn’t push, he knew she’d talk to him when she was ready. Sam wonders for a second if he’s invading her privacy - and just why Dean’s even sent this footage (how did he even  _ get it?),  _ but then he sees Y/N look up from her work, the camera facing her and her desk, so Sam can’t see who had opened her door. 

He sees her mouth moving and she turns and gets out of her chair, walking around her desk and leaning on the other side of it, talking to whoever has entered the room. The picture is fuzzy, still settling as it buffers on Sam’s laptop, so it’s not very clear to him who’s walking closer to her, but they’re brunette, and it’s not someone Sam can identify from the firm - though the picture quality doesn’t help with that. He presses some buttons on his laptop until he manages to unmute the video.

“I’ve told you before, we can’t.” Y/N’s voice fills the large office, and Sam glances up once more to check he’s alone. 

“C’mon, sweetheart, told you before-” Sam’s heart stops in his chest, the picture starting to settle so the quality is better, and he can now see that Y/N is biting her bottom lip as her company steps right up in front of her. 

Dean. 

“He won’t mind. He’d fucking love it. Hasn’t Sammy ever told you how hard it used to make him when I’d fuck his little girlfriends and let him watch?” Sam swallows hard, his eyes wide. No, Sam’s never told Y/N that, he’s always been too ashamed of it. Why is Dean bringing this up now? And then Sam groans a little as he remembers getting drunk with Dean a few weeks back, and making some passing comment about missing those days.  _ Fuck.  _ His cock starts getting hard just thinking about it.

“I don’t believe you, this is some kind of test or something, you’re trying to see if I’d cheat on him, right?” Y/N presses. 

“It’s not cheating when he wants you to fuck me,” Dean points out, and Sam can practically  _ hear  _ Dean’s smirk as he lifts his hand to Y/N’s face and strokes his finger along her jaw, curling it under her chin. 

“He’s not here to watch,” she protests weakly, and Sam can see, even on this small screen, that she’s clinging onto the edge of her desk for dear life, squirming in her heels. 

Dean leans in and whispers something in her ear that’s too quiet for Sam to make out - but whatever it is, it makes Y/N whimper, and when he pulls his face away from her ear, she turns her head and their lips brush. And then they’re kissing, passionate and heated. Sam bites down on his bottom lip and reaches down to grind the heel of his palm into his erection, hoping to stave it off. Maybe he can pause this and watch it later, when he’s at home. But then Dean reaches for Y/N’s skirt and begins to lift it up her legs, pushing his hand between them, making her moan loudly. And instead of closing the video like he knows he should, he eagerly reaches for the buttons of his slacks and gets inside them, pulling his throbbing erection free and wrapping his hand around it. 

It doesn’t take long for Y/N to get on her knees and start sucking Dean down. Dean moans and holds her hair back out of her face, thrusting himself into her mouth, and she grips onto his thighs tightly. Dean’s grunting down at her, telling her how good her mouth feels around his cock, telling her how lucky Sam is to have such a slutty little girlfriend. And then he tells her that he can do it better - gonna make her cum harder than Sam ever has, and Sam’s cock twitches in his palm as he starts to work himself harder and faster. Dean clears Y/N’s desk - enough that she can bend over it, and the camera is the perfect angle to see it all, the way Dean enters her, the way she claws at the desk and screams out in pleasure, and the way Dean grits his teeth when he tells her she’s tight. 

“Bet you’ve never had someone this thick, huh?” Dean taunts. “I’ve seen it, sweetheart, don’t have to pretend I’m not bigger than my little brother. Better at using it too.” 

Sam gasps, bucking his hips up into his hand now as a light swear breaks out over his skin. Y/N’s moans fill the room, and the sound of hips snapping against hips accompanies them. Dean leans down, his mouth pressed to her ear, and he’s murmuring words that Sam can’t hear, and she’s moaning louder than Sam’s ever heard her moan before.  _ Fuck,  _ what is about Dean being better at Sam at this  _ one thing  _ that has him so close to the edge?

“Sam?” He looks up when he realises Y/N is standing in his doorway, eyes wide.  _ Oh fuck, Dean  _ bleeds through the speakers and fills the silence.

Her eyes glass over, “Sam I’m so sorry, Dean told me-” and Sam immediately shuts the laptop, and her eyes drop as she looks to see his hand wrapped around his cock. She licks her lips and frowns, before looking back at his face. “I - so Dean was telling the truth?” she asks. 

Sam bites his bottom lip and pushes back in his chair, beckoning her closer with his fingers. 

“Why don’t you lift up that skirt, sit on my lap, and tell me all about how much you love fucking my brother, whilst I cum in that pretty little pussy, hm?” She chews her bottom lip and nods, stepping towards him. “And you can start by telling me what he whispered to make you cave.” Sam watches carefully as she hitches up her skirt to her waist and pushes her panties down her legs, stepping out of them. She rubs a hand between her thighs and then climbs to straddle his lap in the chair. She’s raised above him as she brings her mouth closer to his ear.

“He told me to put on a show for the cameras - for  _ you.”  _ Sam hums in approval and then chuckles.

“And what a fucking show it was, got me hard as fuck for you. Can’t wait to see it in person next time.” 


End file.
